968-01-4

Basic information

• Product Name: Oxirane, 2,3-bis(4-nitrophenyl)-, (2R,3R)-rel-
• CAS NO: 968-01-4
• Molecular Formula: C14H10N2O5
• Molecular Weight: 286.244
• Mol File: 968-01-4.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: Oxirane, 2,3-bis(4-nitrophenyl)-, (2R,3R)-rel-(CAS DataBase Reference)
• NIST Chemistry Reference: Oxirane, 2,3-bis(4-nitrophenyl)-, (2R,3R)-rel-(968-01-4)
• EPA Substance Registry System: Oxirane, 2,3-bis(4-nitrophenyl)-, (2R,3R)-rel-(968-01-4)

Safety Data

• Hazardous Substances Data: 968-01-4(Hazardous Substances Data)

Upstream product

• 100-14-1 4-nitrobenzyl chloride 
• 83294-14-8 lithium 2,4-dimethyl-3-nitropentan-3-ide 
• 555-16-8 4-nitrobenzaldehdye 
• 619-93-2 (Z)-4,4'-dinitrostilbene 
• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 41570-69-8 1-(4-nitrobenzyl)-tetrahydrothiophenium bromide 
• 100-51-6 benzyl alcohol 
• 619-73-8 4-nitrobenzyl chloride 
• 589-18-4 4-Methylbenzyl alcohol 
• 114841-73-5 diethyl-(4-nitrobenzyl)-sulfonium bromide 
• 736-31-2 trans-4,4'-dinitrostilbene 
• 14688-37-0 cis-p,p'-dinitrostilbene oxide 
• 64-17-5 ethanol 
• 124-41-4 sodium methylate 

Downstream Products

• 13295-04-0 1.2-bis(4-nitrophenyl)ethane-1,2-diol 
• 873420-19-0 α'-iodo-4,4'-dinitro-bibenzyl-α-ol 
• 57507-60-5 2-Methoxy-1,2-bis-(4-nitro-phenyl)-ethanone 
• 736-31-2 trans-4,4'-dinitrostilbene 
• 6067-45-4 4,4'-dinitrobenzil 
• 619-93-2 4,4'-dinitro stilbene 
• 36898-62-1 4,4'-dinitrobenzoin 
• 1033-26-7 4,4'-dinitrobenzophenone 
• 555-16-8 4-nitrobenzaldehdye 
• 129913-30-0 Dimethyl 2,5-bis-(p-nitrophenyl)tetrahydrofuran-3,4-dicarboxylate 
• 129913-32-2 Dimethyl 2,5-bis(p-nitrophenyl)-2,5-dihydrofuran-3,4-dicarboxylate 
• 129913-31-1 2,5-Bis(p-nitrophenyl)tetrahydrofuran-3,4-dicarboxylic anhydride 
• 105222-70-6 α,α'-dichloro-4,4'-dinitro-bibenzyl 

Relevant articles and documents

Unusual reactivity of aryl aldehydes with triethyl phosphite and zinc bromide: A facile preparation of epoxides, benzisoxazoles, and α-hydroxy phosphonate esters

Abstract A facile preparation of trans-epoxides was achieved by a (EtO)3P-ZnBr2-mediated deoxygenation reaction of the corresponding 2-nitrobenzaldehydes. The sterically hindered analogues of 2-nitrobenzaldehyde underwent a reaction

Generation of Sulfur Ylides from Sulfonium Salts and Their Reactions. Comparative Study of Electrochemical Reduction with the Base Method and Mechanism Elucidation by the MO Method

The cathodic reduction of sulfonium salts in acetonitrile in the presence and absence of benzaldehyde was carried out. Results were compared with results of the base method. In the presence of benzaldehyde, the electrochemical reduction gave epoxides as a result of the Corey-Chaykovsky reaction, thus confirming ylide formation. The electrochemical reduction of sulfonium salts without benzaldehyde yielded rearrangement products in high yield. On the contrary, upon base treatment of sulfonium salts without benzaldehyde, symmetrical epoxides derived from the benzyl group of the sulfonium salt are obtained as main products as a result of the auto oxidation of the sulfur ylide. The reaction mechanisms were elucidated based on the results obtained by a semi-empirical molecular orbital method.

Experimental evidence for multiple oxidation pathways in the (salen)Mn-catalyzed epoxidation of alkenes

The substrate electronic effects on the selectivity in the catalytic epoxidation of para-substituted cis stilbenes 2a-i were investigated by using (R,R)-[N,N′-bis(3,5-di-tBu-salicylidene)-1,2-cyclohexanediamine] manganese(III) chloride 1 in benzene as the catalyst with iodosobenzene as the terminal oxidant. A Hammett study of the selectivity results reveals a stronger electrophilic character than previously assumed in the (salen)Mn-catalyzed reaction. In general, the best correlations with the experimental values were obtained by using the Hammett σ+ values, which gave ρ = -1.37 for the rate of cisepoxide formation and ρ = -0.43 for the rate of the stepwise process leading to the corresponding trans product. The reaction involves two separate pathways as indicated also by the competitive breakdown of the intermediate on the path to trans epoxide for methoxy-substituted substrates. The asynchronicity in the concerted pathway leading to cis epoxide is apparent for 4-methoxy-4′-nitrostilbene, which yields cis epoxide with 75% ee entirely as a result of electronic effects.